Water → HCID 68231919, compound

HRID 1465820Notes

Reaction equation

HRID 1465820 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH:8]=1)[NH2:7].[CH3:12][O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][NH2:19].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C(=O)C>[CH3:12][O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][NH:19][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([NH2:7])[CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 742185-Chloro-2-nitroanilineHCID 5205302-(2-Methoxyethoxy)ethanamine

Product 1

HCID 68231919HCID 68231919, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 5-chloro-2-nitroaniline (1.6 g, 9.3 mmol), 2-(2-methoxy-ethoxy)-ethylamine (2.0 g, 16.8 mmol) and anhydrous potassium carbonate (1.38 g, 10 mmol) in N,N-dimethylacetamide (3 ml) was stirred at 120° C. under nitrogen for 3 days. Sample NMR analysis showed 80% conversion of the starting material. The resultant mixture was then cooled to room temperature, poured into cold water (30 ml) and extracted with ethyl acetate. The organic extract was washed with brine, dried and evaporated. The resulting orange yellow oil was subjected to a silica gel filtration on a 5 cm×6 cm silica gel plug, eluting first with 50% ethyl acetate/petroleum spirits (40-60° C.), followed by 100% ethyl acetate. Evaporation yielded an orange-red liquid, 1.1 g (45.8% yields).

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe organic extract
  3. washwas washed with brine
  4. customdried
  5. customevaporated
  6. filtrationThe resulting orange yellow oil was subjected to a silica gel filtration on a 5 cm×6 cm silica gel plug
  7. washeluting first with 50% ethyl acetate/petroleum spirits (40-60° C.)
  8. customEvaporation
  9. customyielded
  10. customan orange-red liquid, 1.1 g (45.8% yields)

Sources & evidence

ORD record
ord-79157456c8a44ec399af56dd31028029
Source dataset
uspto-grants-2015_04
Patent number
US08999993B2

Reaction notes

Loading…